


Fantasy Come True

by Inell



Category: Teen Wolf (TV)
Genre: Anal Fingering, Anal Sex, Aromantic Jackson, Bottom Derek Hale, Cock Rings, Deputy Derek Hale, Deputy Stiles Stilinski, Derek and Stiles have Jackson join them for one night, Derek has a fantasy, Derek is shy, Dirty Talk, Double Anal Penetration, Established Derek Hale/Stiles Stilinski, Fantasy Fulfillment, Kissing, M/M, Multi, Oral Sex, Praise Kink, Rimming, Romance between Stiles/Derek, Sex Toys, Threesome - M/M/M, stiles is not, they are too adorable
Language: English
Status: Completed
Published: 2016-01-27
Updated: 2016-01-27
Packaged: 2018-05-16 18:19:58
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 7,412
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5835985
Author URL: https://archiveofourown.org/users/Inell/pseuds/Inell
Summary: <blockquote class="userstuff">
              <p>Derek and Stiles are always fulfilling fantasies off of Stiles' Bucket List of Fantasies, but Derek's always too shy to admit any of his. One night, Stiles finally finds out something Derek really wants to do. He enlists the help of Jackson to make Derek's fantasy come true.</p>
            </blockquote>





	Fantasy Come True

**Author's Note:**

  * For [alisvolatpropiis](https://archiveofourown.org/users/alisvolatpropiis/gifts).



> For alisvolatpropiis' prompt: established relationship Sterek, with Stiles asking Derek to share his fantasies, and after much coaxing, a blushing, shy Derek admits that he's dying to get DP'd, and because he is the best boyfriend ever, Stiles invites Jackson (an ex of his perhaps?) to give Derek his fantasy. 
> 
> I really hope you enjoy this, hon! <3 Thanks so much for the lovely prompt!

The sound of heavy breathing against his ear is the first thing Stiles becomes aware of as he comes down from his high. His cock is still twitching inside Derek, tight heat clenching around him as Derek keeps slowly riding him. There’s sticky wet on his belly and chest from Derek’s come, and he knows it must be sticking to Derek’s chest hair, but neither of them really care that much at the moment. He strokes his fingers down Derek’s spine, feeling damp skin slick with sweat, and he mouths at Derek’s shoulder as he lazily pushes up inside him.

“Wow.” Stiles finally says, breaking the blissful silence when Derek finally stops moving and just collapses on top of him. “That was…intense.”

“Mmm.” Derek just moans against his neck in agreement, stroking his hands down Stiles’ arms until their hands are clasped together. “Yeah, it was.”

“Thank you.” He nuzzles Derek’s neck and face until he turns his head so they can share a kiss.

“I, uh, enjoyed it.” Derek is surprisingly shy when it comes to talking about sex. It’s adorable, really, and Stiles respects his boundaries. It works out relatively well anyway, because Stiles likes to talk, especially dirty, and Derek has learned that there’s no judgement when he _does_ vocalize his desires.

“You played the bad cop so well, babe,” Stiles says, kissing Derek’s cheek then his jaw. “I really believed you were going to take me to jail.”

Derek groans, the top of his ears flushing with heat. “I’m never going to be able to look at our uniforms the same, you realize?”

“Hey, I’m the one who got fucked by my baton,” Stiles points out with a big grin. “You got to be the hot ass deputy willing to let me exchange sex for a get out of jail free card. Anyway, our uniforms have always turned you on. Don’t lie.”

“Maybe so, but you’re the one who has spent the last three years trying to get me to roleplay wearing them.” Derek rubs his chin against Stiles’ neck, his beard brushing against his skin just enough to make a mark.

“And you finally did, and we had amazing orgasms. It’s a win all around, I think.” Stiles runs his fingers through Derek’s hair. “Another fantasy marked off the bucket list.”

“You and your bucket list of fantasies.” Derek’s laugh is a huff of warm air on Stiles’ sensitive skin.

Stiles just smiles. “You know you love it.” Derek doesn’t disagree as he finally moves, letting Stiles’ spent cock slide out of his ass. They’re a mess, which isn’t too surprising considering how into the roleplay they got by the time it finished. Stiles’ dick is actually sore from coming so much, and his ass has that nice ache from being well fucked. He reaches up to grip Derek’s hair and pull his head down for a kiss. When they part, he looks into Derek’s eyes and whispers, “You know, you can add anything to _our_ bucket list that you want. It’s not just my bucket list.”

“I know.” Derek kisses his forehead before crawling to the side of the bed. “I think your imagination is enough for both of us.”

Stiles frowns the way he always does when they broach this topic because he knows Derek is lying. He doesn’t have to be a werewolf to realize that Derek isn’t being completely truthful, after all. There’s always an avoidance of eye contact, a tongue quickly swept across a bottom lip, and Derek being really uncomfortable whenever he’s asked to name some of his fantasies. The uncomfortable part is why Stiles always lets the subject drop because the last thing he wants to do is make Derek feel that way. But he also doesn’t like the idea that Derek doesn’t feel like he can be open about his inner most fantasies, especially when Stiles is entirely too candid about his, and Derek is always so accepting about them. Even the things they discuss and decide aren’t worth trying outside of discussion for whatever reason.

Tonight, though, Derek has finally made one of Stiles’ dirtiest and longest running fantasies come true. He’s wanted to roleplay cop and perp since Derek first became a deputy the latter part of his senior year of high school, nearly five years before they even started dating, and it’s only got worse since he became a deputy, too. It’s taken him three and a half years of dating and then becoming serious before Derek actually suggested they try it. Stiles is now in a freaking awesome mood and loving Derek even more than usual, which shouldn’t be possible since he already loves him so fucking much it’s ridiculous, and he just wants to give Derek that same pleasure of having something he secretly wants coming true.

“I’m gonna go take a shower,” Derek says, standing at the dresser and scowling in the cutest way ever down at the come drying in his chest hair.

Stiles is so going to find out one of Derek’s favorite fantasies, he vows then and there, and it isn’t going to be easy, but he isn’t going to let it just drop this time. With that in mind, he rolls off the bed to follow Derek to the bathroom, not bothering to get clean underwear from the dresser. They live alone, and Derek likes his junk, so it doesn’t matter if it’s covered or not. Derek’s already got the water on, and he looks up with a sly smile when Stiles enters the bathroom. “Gotta conserve water, don’t you know?”

“Right. Since you’re here, you can wash my back then.” Derek has a thing for Stiles washing his hair and taking care of him, and, well, it’s Stiles’ thing now, too. He steps into the shower behind Derek, reaching for the shower gel that Lydia bought them for Christmas. “No shower sex, Stiles.”

“Moi? Shower sex?” Stiles scoffs. “Well, I never.”

“Lie.” Derek laughs as he turns to face the spray, tilting his head back slightly.

“Not tonight, it isn’t. I think my dick is exhausted.” Stiles rubs his hands together to get the gel sudsy before he starts to touch Derek’s bare back. “You were also rather, uh, forceful with that baton, so my ass is sore. In the best way.”

“Sorry. You were just making those noises, and I got carried away.” Derek glances over his shoulder at him. “You should have told me to stop. I don’t want to hurt you.”

“Derek, what part of ‘best way’ don’t you understand?” Stiles leans over to kiss Derek’s shoulder. “I liked it. You know I never complain when you get a little rough and let your control go.”

“I know. So do all our friends,” Derek reminds him dryly, giving him a small smile before turning back to face the spray.

Stiles uses his long fingers to his advantage as he rubs the gel into Derek’s skin, tracing the curves of his tattoo and giving a lot of attention to his ass. “What do you fantasize about?” he asks quietly, stroking his fingers over the swell of Derek’s gorgeous ass.

“You.” Derek tenses slightly and ducks his head, that familiar uncomfortable tension coming back. “All I ever want is you.”

“Well, yeah, same here. I wouldn’t want to do all the stuff we do with anyone else,” Stiles agrees, moving his hands to Derek’s ribs then down his legs. “But me doing what?”

“Stiles, I’ve told you before, everything you talk about turns me on. I don’t really think the way you do, so it’s not like I’ve made lists since I was thirteen and realized what my dick was for,” Derek mutters, a slight edge of anger in his tone at being pushed this way.

“Turn towards me, babe. I need to get your front.” Stiles isn’t sure Derek is going to do it, but he finally does, keeping his attention on the bathtub instead of Stiles. The tops of his ears are starting to redden, which means he’s embarrassed. Stiles sighs as he gets more gel into his palm. “I just want to make you feel as wonderful as you do me when we have a play date. You make my dreams come true, you know? I’d just like to return the favor sometime.”

“You place too much importance on sex.” Derek glances at him then, a faint blush high on his cheekbones. “Just being with you, whether we’re fucking or working a case or watching Netflix, you make every dream that I never thought I’d actually have come true. All I need to be happy is you.”

“I love you.” Stiles leans in for a kiss, so proud of Derek for being able to say all that without getting nervous or shutting down. They’ve come so far over the years, and he isn’t going to risk that by pushing too much. But he can’t let it go until he knows for sure Derek realizes he can be honest about what he wants sexually. Hell, it had taken months before Derek even admitted he liked being fucked and really got off on Stiles holding him down and wrecking him.

When they pull apart, Derek is smiling. “See? That’s better than any perverse fantasies,” he points out, rubbing their noses together as the warm water continues to spray.

Bingo. “No fantasy is perverse,” he says casually, focusing on soaping up Derek’s chest, possibly paying more attention to his sensitive nipples than is appropriate for a no sex shower. “I mean, hell, I told you about how often I used to jerk off thinking about being gang banged by the lacrosse team. Wouldn’t actually want to do it…well, not now obviously…but it’s still something I fantasized about. And you didn’t judge me.”

“I hate to tell you, Stiles, but that _was_ rather perverse.” Derek keeps his face stoic, his voice deadpan, but there’s humor in his eyes when Stiles makes a face at him.

“Yeah, well, you let me give you a blowjob during the pack Thanksgiving dinner, despite your initial hesitation, and there was no judgment there, either.” Stiles decides it’s time to stop playing fair. He moves his hands down Derek’s chest, making sure that his hipbones and delicious thighs are covered with suds before he casually focuses on his groin and dick.

“I think I can wash that myself.” Derek’s eyes are already half-closed, his lips parted, and Stiles has only just begun. Stiles 1, Derek 0 in the battle of fantasy admissions.

“Nah, I can handle it.” Stiles caresses Derek’s balls with his palm, making sure to get every bit of flesh covered in soap. “When you’re lying in bed jerking off and thinking the dirtiest things to get you off, what do you think about? What fantasy gets you so hot that you almost come without even touching yourself?”

“Stiles, don’t make me,” Derek whines, full on blushing as he bucks into Stiles’ hand, looking so shy and confused that Stiles immediately feels bad for pushing.

“Fuck. I’m an asshole.” Stiles smiles wryly before he kisses Derek, jerking his hand with intent instead of teasing, listening to Derek’s breathing falter as he comes. After, he focuses on actually cleaning Derek, even washing his hair as a silent apology for being such a demanding prick sometimes.

It’s when they’re lying in bed after, hair damp but bodies dry, Derek curled against him with his beard lightly rubbing against his neck, that Derek whispers in his ear, “I want you to fuck me with someone else. Both of you, at the same time.”

Stiles’ eyes widen because, hello, that’s not even something on his own list, and he can see that the top of Derek’s ears are so red it’s ridiculous, so he really means it. The idea of another man seeing Derek naked, of sharing Derek, it bothers him a little bit, to be perfectly honest, but he isn’t opposed, depending on the guy. It isn’t a question of insecurity, he knows he and Derek are the forever kind of thing, but there’s some jealousy at the thought that surprises him. He kisses Derek’s shoulder and strokes his hair. “You want to be full, babe? Unable to move as you’re caught between us?”

“Stiles,” he whimpers, teeth scraping against his neck. “Don’t…don’t talk about it.”

“You have to look at me,” he says quietly. He keeps stroking Derek’s hair until he finally raises his head. “If you really want to do this, I’ll arrange it. But I get to pick the guy because, well, I don’t want my jealousy fucking up your fantasy.”

“I…really?” Derek blinks at him, a shy smile on his face as he touches Stiles’ jaw. “I don’t care about the guy. Just his cock. And, uh, yeah…I think I might…it would be…could we?”

“Yeah, we can do it. We’ll have to use a toy on you first, slide it in you along with my dick, make sure you can handle it, that you won’t get hurt, then we can bring in a guy and use his dick for sex.” Stiles knows he’s going to do everything in his power to give this fantasy to Derek and make it amazing. 

Now he just has to find the right guy.

**********

It’s not as easy as originally expected to find the perfect guy. Stiles immediately rules out a stranger because he knows there’s no way Derek’s going to allow some stranger to have him in a vulnerable position. No, it needs to be someone they know and trust. That limits the possibilities greatly. Scott is a definite no. While Kira is certainly likely to agree, probably would want to watch, Scott’s the alpha, and that adds a level of complexity they really don’t need for a one-time thing. Besides, it’s Scott. Stiles isn’t really that interested in seeing him naked or having their dicks in his boyfriend’s ass.

He crosses Liam, Brett, and Jordan off the list for various reasons including extreme heteronormative tendencies, a jerk personality, and enough risk of jealousy to avoid even trying. Mason might be willing, but he’s a nice guy, so Stiles doesn’t want to turn him into a sex toy. Chris is definitely a dick hardening possibility, but he’s also an Argent, so no. Just no. There’s really only one real choice, not that Stiles is going to let on that he ruled out everyone else first. It’s not like Jackson isn’t his first thought, but he has to consider all options before deciding to involve his former friend with benefits with his current sex life.

When Stiles arrives at the coffee shop near the station, Jackson is already there drinking some concoction with too much foam and cream. Fortunately, he got a table in a corner that isn’t near anyone else, so they can talk without risk of being overhead. Stiles nods at Jackson before going through the line and getting his own coffee. He walks over to the table, rolling his eyes when Jackson gives him a lazy smile and appreciative look over. “That uniform looks good on you, Stiles.”

“You like?” He does a little turn, shaking his ass, then sits down. “Thanks for meeting me, Jax.”

“Are you dying?” Jackson arches a brow and studies him. “You’re being too nice. You’re either dying, or you know that _I’m_ dying, or you want something.”

“You’re so suspicious. I can be nice. I remember quite a few nights when you told me just how nice I could be,” Stiles reminds him, kicking his leg under the table. “No one is dying.”

“Then you want something.” Jackson smirks, seemingly enjoying the fact that Stiles needs a favor. He’s going to be an insufferable prick about all this, Stiles already knows it. “What is it?”

“Not so fast. I need you to make me a promise that our conversation won’t go any further than this table.” Stiles looks at him seriously, wanting him to know that he’s not joking around.

Jackson’s smug look fades, and he sits up straighter. “Is Derek dying?”

“Dude, no one is dying.” Stiles groans. “Promise.”

“Are you leaving him?” Jackson’s eyes widen before he snorts. “Yeah, nevermind. You’re both too happy for that. Sure, I promise nothing we talk about will be repeated. You know I can keep secrets.”

“Yeah, I do.” Stiles taps his fingers against his cup and tries to remember if he took his Adderall this morning. With a slight shake of his head, he focuses. “I want you to fuck Derek with me.”

Jackson chokes on the mouthful of coffee in his mouth. When he can finally breathe again, he hisses, “What? Is this a joke?”

“Nope.” Stiles starts tapping his foot. “There’s this thing we do, fantasy fulfillment, and Derek is always so giving and never takes, and this is something he wants. I figured you’d be the best guy for the job.”

“Just once, right? Not some sort of relationship thing?” Jackson makes a slight grimace at the word relationship.

“God no. It’s just a night of sex. In fact, we’ll pretty much just use you as our sex toy, and I know how that tends to get you off, so you should enjoy it.” Stiles waggles his eyebrows.

“Sure.” Jackson’s agreement is almost too quick and easy. Stiles frowns and studies him a moment. “What? I’m single, it’s been longer than I care to admit since I got laid, and fucking two hot guys is better than trolling a club for a blowjob in the bathroom. Honestly. Did you really think I’d say no?”

Stiles shrugs. “I just thought it might take more persuasion.”

“What can I say? I’m easy when it comes to you,” Jackson admits, giving him an almost affection smile before he becomes cocky again. “I do have some conditions, though.”

“What kinds of conditions?” Stiles licks caramel off his lip before taking another drink of his coffee.

“Don’t get your emotional shit on me. I’m there for sex, not all the lovey dovey crap you two do together. I want you to fuck me at some point. I miss your cock, so I’m totally taking advantage of this opportunity to have it again. And, last, we never speak about it to anyone because no one else needs to know about it. That means McCall, too.”

Stiles considers it and decides they’re fair conditions that Derek isn’t likely to dispute. “I don’t tell Scott details about our sex life, so that’s not even a problem. As for the other stuff? Totally doable. You’d better just not fall for us. I know you still regret not locking all this down when you had a chance.” He motions at himself and grins.

“Right. I cry myself to sleep every night because I lost you to Derek,” Jackson deadpans, lightly kicking Stiles’ leg. “So, when are you planning this fuck fest?”

“We’d already stopped our fuck buddy thing when Derek and I realized our feelings were mutual, so none of that losing me bullshit,” Stiles reminds him. “Is Friday night good for you? Derek and I are both working day shift, and we’re off this weekend for once, so there’ll be time to recuperate.”

Jackson pulls out his phone and taps on it for a moment before he nods. “I’m clear Friday night. What time? I’ll put in my calendar.”

“Say eight? We’ll feed you first, since you’ll need the energy.”

“Like I won’t be able to keep up with you, asshole.”

“You’d be surprised, shithead. We’ll wear your ass out.”

“No, it’ll be your boyfriend whose ass is worn out.”

“Don’t leer like that. It’s ridiculous. And I seem to remember another ass being mentioned in negotiations.”

“If you dare gloat about me missing that thick cock of yours, I’ll have to change my mind, and you’ll be stuck begging McCall for some skinny old alpha cock.”

“Been staring at Scott’s dick a lot, Jax?”

“Please. I was a bisexual teenager on an athletic team. _Of course_ I looked at other guys in the showers. It’s the only reason you were even slightly tolerable. Well, that and those lips of yours.”

“You’re such a size queen,” Stiles mutters fondly. He isn’t even huge or anything, but Jackson always made him feel like a fucking porn star. The sex between them had always been awesome, but he’s too clingy and needy for someone like Jackson, who doesn’t really like mixing sex with emotion. He keeps them separate, and Stiles doesn’t judge him for it.

“Not my fault your cock is so thick and just long enough to touch all the right spots.” Jackson shifts in his chair like he’s remembering the feel of it in his ass. “I’ll be there at eight. Make that chicken pasta dish I love.”

“I’ll think about it.” Stiles finishes his coffee and glances at his watch. “Damn. I’d better get back to the station.” He stands up and reaches over to grip Jackson’s shoulder. “Thanks for doing this, dude. See you Friday.”

**********

The pasta is just about finished, and the chicken is waiting to be added to the pot. Stiles has the sauce ready, so there’s nothing much left to do except wait. Derek is working on the salad, his shoulders and back tense as he slices the knife through the tomatoes. He’s wearing a soft gray Henley that fits him so well that it makes Stiles’ fingers itch to touch, and his jeans are snug across his ass. Stiles’ gaze lingers there as he thinks about their efforts to get him ready for tonight. It’s been such a turn on to increase the size of the dildos, to get Derek accustomed to being so full, to feel the toys against his dick as he fucks both things into Derek.

This is Derek’s fantasy, but Stiles has to admit that he’s excited for tonight, too, because he wants to watch Derek as another cock moves inside him. Wants to see his face as he’s stretched so wide and stuffed so full. Wants to see his eyes as his fantasy comes true. Stiles knows he’s going to be so beautiful, and he’s ready to talk him through the whole thing so it’s a wonderful experience for him. As for him, well, the toys are okay, but it’s not the same as another cock, not warm and fleshy and wet. He really can’t wait to feel Jackson’s dick rubbing against his as they fuck Derek. It probably also helps that it’s Jackson joining them, so he isn’t feeling jealous or threatened because Jackson isn’t going to get weird about it. He’s about the sex and nothing else.

“Are you staring at my ass again?” Derek’s tone is amused and knowing. “I can smell your arousal, and your heartbeat is steadily increasing.”

“It’s your fault for having such a great ass,” Stiles points out, walking up behind Derek and resting his chin on his shoulder. He wraps his arms around his waist and squeezes. “You still good with all this?”

“Yeah, it’s all good.” Derek turns his head and kisses his nose. “I’m glad it’s Jackson, though.”

“I wasn’t sure if that might make it awkward for you, considering my past with him.” Stiles nuzzles Derek’s cheek, his soft beard rubbing against his chin.

“That actually helps. I know there’s no risk of you enjoying him so much that you’ll try to leave me,” Derek admits. “I know you wouldn’t, so don’t even get defensive. It’s just…I’m a little jealous at the idea of some other man touching you, having you, and I know it’s irrational, but whatever.”

“That’s alright, babe. I’ve thought the same thing.” Stiles laughs. “I think we’re probably both a little too possessive to ever think about becoming swingers.”

Derek lets out a low growl and his eyes flash blue. “That better not show up on that bucket list of yours.”

“Dude, why would I want anyone else when I’ve got you?” Stiles snorts. “No worries about that from me ever.”

Before Derek can respond, there’s a knock on the door. Derek sniffs the air. “It’s Jackson, and he’s already aroused.”

“Guess it’s a good thing dinner is almost ready. We won’t have to wait long for dessert.” At his words, Stiles squeezes Derek’s ass as if to indicate exactly what dessert is going to be tonight.

“Go answer the door,” Derek says, rolling his eyes even as the tops of his ears turn red.

Stiles obeys, opening it to find Jackson standing there looking pretty damn good and holding a bottle of wine. “It’s for you, since Derek and I can’t get drunk off it,” Jackson announces, moving his gaze deliberately up Stiles’ body and smirking. “You stink of arousal.”

“Don’t get so cocky, asshole. Derek could smell you through the door, so I’m not the only one.” Stiles takes the wine and shuts the door behind Jackson. They go into the kitchen so he can finish dinner. “I’m making that chicken pasta you like so much.”

“I feel so special,” Jackson deadpans. “Derek, good to see you.”

“Jackson.” Derek nods at him, straightening his shoulders and keeping his head raised. “Go ahead and get it over with.”

“What?” Jackson bats his eyelashes. “I was just wondering if you had any _double stuffed_ Oreos around.”

“Play nice or you can leave,” Stiles says in a sing-song tone, giving Jackson a warning look so he’ll know he’s serious.

“I always play nice, Stiles.” Jackson smirks. “You should remember that much. It hasn’t been that long.”

“Long enough.” Derek turns to face Jackson and crosses his arms, which makes his shirt pull snugly against his biceps. Stiles is distracted from the conversation for a moment. When he listens back, Derek is still talking. “You can either be part of this or you can leave and we’ll find someone else.”

Jackson stares back, eyes flashing a moment before he ducks his head and bares his neck in submission. Fuck, that’s really hot. “I want to do it.”

“Good.” Derek looks him over. “Stiles has been telling me about your cock all week. I’m curious to see if you’re as good with it as he claims.”

“Probably better. He never gives me enough credit.” Jackson walks past Stiles and steals a piece of the cut up chicken. “Can we eat yet? I’m starving, and it’s been years since you’ve made this for me.”

There’s still a tension in the air, but it’s more of an excited tension. It lingers throughout dinner, as they catch up with each other and Jackson talks about his random conquests who don’t seem to understand that he keeps his sex life and his personal life separate. Well, usually, but Stiles always seems to be the exception there, mostly because he can separate it, too. By the time they finish eating, half the bottle of wine is gone, and they’re starting to exchange looks and touches that linger as they talk. The tension is still excited, but it’s definitely moving towards sexual as every minute passes. Finally, Stiles knows it’s time to move things to the bedroom.

“Is everyone ready for dessert?” he asks with an innocent smile. “If so, let’s get this stuff cleaned up so we can go get naked.”

“We’ll wash up. You did most the cooking,” Derek tells him. “Jackson, get the plates.”

“Why should he get to sit around?” Jackson asks even as he obeys. Derek might not be the alpha anymore, but he’s obviously still one in Jackson’s mind. It’s pretty fucking hot because Stiles hasn’t really noticed it until tonight.

“He isn’t going to sit around,” Stiles points out, getting up to help. “The sooner we get done, the sooner we get to fuck, after all.”

“Sometimes I feel like I’m in love with a horny teenager.” Derek shakes his head and rolls his eyes when Stiles just grins at him. 

“You know you love me.” He leans in for a kiss before shooting a glare at Jackson, who is mock gagging. “Keep that up, and I’ll get my emotions all over you, dickhead.”

Jackson shudders. “God, not that. Anything but that.” He smiles slightly as he scrapes the plate in the trash before handing them to Derek to be washed.

Stiles makes up two containers with leftovers, one for them and one for Jackson to take with him, then he nudges Derek over so he can clean the pots. When they’re all finished, he grabs each of them a bottle of water so they can stay hydrated, and then leers at them. “C’mon boys. It’s time for dessert.”

Derek just groans. “That isn’t any sexier now than it was earlier.” He takes the bottle of water Stiles offers him and then heads down the hall towards their bedroom.

“He’s got such a great ass,” Jackson whispers, both of them watching Derek walk away.

“I heard that,” Derek reminds them, shaking it just a little before disappearing into their bedroom.

“We’d better go before he gets started without us.” Stiles hands Jackson his water then takes off down the hall, sliding on the wood floor in his socks. When he enters the bedroom, he sees Derek sitting on the edge of the bed looking nervous. “Hey, none of that. If it gets to be too much or you change your mind, we’ll stop. Alright?”

“I know, it’s just actually happening now and I’m realizing that, I guess.” Derek tugs him closer and rests his cheek against his chest. “Jackson, stop lurking in the doorway. We aren’t going to bite.”

“Oh, haha. Wolfman has jokes,” Jackson mocks as he steps into the bedroom. He kicks off his shoes before looking around, sniffing the air as his eyelids flutter shut. “God, that smells good.”

“Wait until you smell it fresh,” Stiles says, assuming he’s talking about whatever sex smells still linger in the room. He’s brushing his fingers through Derek’s hair, trying to relax him enough so he can start enjoying this instead of freaking out. “Babe, how do you want us to start this? It’s your fantasy.”

“Stiles, don’t make me talk.” Derek looks up at him even as a flush spreads across his cheekbones. “You can take control. I trust you.”

“Okay.” Stiles slowly nods, trying to think of the various options. “Jackson wants me to fuck him, so why don’t we start with that? Then I can get you ready and we’ll fuck you?”

“Yeah. That’s good.” Derek clears his throat and he licks his lips.

“Is all the blabbering done now? I want to get naked.” Jackson pulls his shirt over his head and throws it on Stiles’ comfy reading chair. “If my vote counts, I want to suck Derek’s cock while you’re fucking me, Stiles.”

Derek makes the softest noise at that, almost a whimper, and Stiles smiles. “Sounds good.” He steps away from the bed and begins stripping, moving his gaze between Derek and Jackson as they both get naked. He’s already half-hard by the time his clothes are on the floor around him. Since he’s not stupid, he knew tonight would be a test of his stamina, so he bought something when they picked up the toys for Derek that should help. He grabs the cock ring out of the drawer and takes it over to Derek. “Why don’t you get me ready then put this on me, babe? Jackson, get down here and put your mouth to work. Help him out.”

Jackson stares at Stiles’ dick and smiles. “With pleasure.” He walks over and drops to his knees beside Derek, and they both begin licking the sides of Stiles’ dick. It’s almost funny how different they both are in their approach, gentle teasing licks from Derek and intense sucks from Jackson. Looking down at them, he realizes he actually can mark another thing off his bucket list, even if it’s not a fantasy he’s ever mentioned before because he never thought it would happen. Having two hot guys on their knees sucking his dick is sloppier than he expects, but it’s still pretty fucking amazing.

When he’s completely hard, Jackson pulls off his dick and then paints Derek’s lips with pre-come. Stiles moans deep in his throat as he watches, fingers gripping Jackson’s hair in the way he knows he enjoys. “Good boy,” he murmurs, watching Jackson’s face flush even as he can’t help preening. “Derek, put the ring on me now, okay?”

“Yeah. I can do that.” Derek’s fingers are shaking slightly, from nerves or arousal or both, and he fumbles a bit before he manages to secure the leather in a way that will help Stiles keep his erection until he needs it later. While he could probably get hard again eventually, he doesn’t want to risk not being able to perform for Derek.

“Thank you,” Stiles says, brushing his fingers through Derek’s hair and rubbing his scalp. “Jackson, get on the bed. On all fours.” He watches Jackson obey, admires the firm ass and curve of his back. “Babe, you wanna get him ready for me?”

Derek looks at Jackson then back at Stiles and nods. “I’d like that.” He gets up and crawls onto the bed behind Jackson, spreading his cheeks before leaning down to lick a swipe from his balls to his hole. Jackson gasps, fingers already clenching the blankets.

“That’s good, Derek. Keep licking him, make him whine.” Stiles moves behind Derek, arching a brow when he sees one of the butt plugs in his ass. “You’ve had that in you all this time?”

“Wanted to get ready for tonight,” Derek admits, looking almost shy as he glances at Stiles. Jackson’s ass is already reddening from Derek’s beard, the sensitive skin a pretty flushed color as Jackson offers his ass to whoever wants it. “I thought you might enjoy the surprise.”

“I do, babe. You’re so good to me,” he says, rubbing Derek’s ass cheeks and smiling at him. He grips the end of the plug and slowly eases it out of Derek’s ass, watching him clench around it, trying to keep it inside. He thrusts it back in, rewarded with a grunt from Derek as he uses his tongue to make Jackson beg. Stiles lazily fucks Derek’s ass with the plug, squirting a little more lube on it as he watches his boyfriend eat out Jackson’s ass. “Use your finger now. Give him two at once. He likes it when you make him take it.”

“Oh fuck,” Jackson gasps, back arching so prettily. “Damn it, Stiles. Fuck me. I’m past ready.”

“Toys don’t get to make demands.” Stiles grins as Jackson whimpers, fingers gripping the blanket so hard that he’s surprised it hasn’t torn or been shredded by claws. “Keep fucking him, Derek. You’re doing so good, babe.”

Derek’s breath catches when Stiles reaches under him to begin stroking his dick. It’s warm in his hand, throbbing, dripping pre-come, so, yeah, he’s definitely enjoying this. He might not be able to say the words, but his body talks enough for Stiles to understand. He licks Jackson’s hole, using his tongue to fuck him then pushing three fingers inside, stretching him, drawing out beautiful noises.

“Please,” Jackson whispers, voice hoarse and broken. “Please, please fuck me, Stiles. I need you so bad. Please.”

Stiles looks at Derek and nods. Derek moves, letting Stiles take his place. He strokes his hand up Jackson’s back as Derek squirts some of the lube on his dick and then drags his hand down it to get him wet. “It’s okay, Jax. I’m here. I’m gonna take care of you,” he murmurs soothingly, watching as Derek takes his dick and aims it into Jackson’s hole for him. He kisses Derek as he slides into Jackson, groaning lowly when tight heat clenches around him. Jackson is babbling within a half dozen strokes, pushing back against him, mouth open and face flushed. “Go fill his mouth, Derek.”

Derek smiles as he crawls up the bed and pulls Jackson’s head back. “Open wide, Jackson,” he says before he pushes his dick halfway into his mouth. Jackson begins to move his head, sucking Derek’s dick as Stiles keeps fucking him with slow deep strokes. Stiles leans forward to kiss Derek, licking into his mouth as Jackson writhes between them. It’s so fucking hot and, yeah, another thing marked off his super secret bucket list of fantasies monogamous couples don’t usually get to fulfill.

Jackson comes without anyone even touching his dick. He just pushes back hard and his body tenses before he’s shuddering, soaking the blanket with his come while taking Derek’s dick all the way down his throat. Since Stiles has the cock ring on, he isn’t going to come, but he knows he would have by now because Jackson is so tight and watching Derek get his dick sucks is really hot. He pulls out of Jackson’s ass and reaches for their water, tossing the bottles to each of them. “We need to hydrate before moving forward. The smell of sweat is so heavy that even I can smell it.”

“Smells good with the scent of come and sex,” Jackson says, voice even more hoarse after his throat has been fucked. He gulps down water before tossing the closed bottle back on the side of the bed.

“I’m ready, Stiles.” Derek licks his lips. “I want you both to fuck me now.”

“You’re sure?” Stiles gives him the chance to change his mind, but he isn’t surprised when Derek just gives him a look that totally says ‘dumbass’ without him having to say a word. The eyebrows speak for him. He rubs Jackson’s head, giving him the praise he needs before he shifts around until he’s sitting on the bed, avoiding the wet spot Jackson left. He unfastens the cock ring, grateful for the immediate relief, and then smiles at Derek. “Come ride me, Derek.”

Derek reaches behind him and pulls out the plug, tossing it on the floor so they can wash it later. He straddles Stiles, ignoring the bottle of lube Jackson offers, and he begins to push down. His eyes close and his head tilts back as he gradually takes more of Stiles’ dick.

“So beautiful,” Stiles murmurs. “Love to see you like this.” He reaches out to stroke Derek’s chest, fingers brushing through whorls of chest hair, thumb rubbing his nipple. “So good for me. Take it all. So tight around me.”

“Fuck,” Jackson sighs, fingers stroking his dick as he starts to harden again. Jackson always has a quick recovery time, which is the only reason Stiles let him come before they fucked Derek. “Look at him take it.”

“He’s so good,” Stiles says, smiling at Derek when he gives him that shy but pleased look he often gets during one of Stiles’ sex induced rambles. “Fuck yourself on my dick, Derek. When you feel ready for more, let me know.”

“Okay.” Derek begins to ride his dick, palms on Stiles’ chest as he bounces up and down. It’s already so good that Stiles isn’t sure he’s going to last long enough for Derek to really enjoy it when Jackson joins them. Derek moves for a dozen or more strokes, dick still hard and leaking, swollen almost purple now because he’s so close but trying to fight it off. “I think I’m ready.”

“Jackson, get the lube. Coat your dick and use just a little on Derek’s hole. Go slow, and if he says stop, you stop,” Stiles says, stroking Derek’s arms and watching his face as Jackson’s wet fingers are suddenly pushed into his ass alongside Stiles’ dick. Derek whines, a low whine that sounds like it’s been ripped from his throat, and his face twists into a wrecked look of pleasure that makes Stiles’ dick throb. Jackson scrambles into place, obviously affected by Derek’s noises just like Stiles, and soon there’s another dick trying to push into Derek’s tight ass. “Relax, babe. You have to relax and let him in.”

“Too much,” Derek mutters, his fingers curling into his palms as Jackson keeps trying to push inside. “Oh God, Stiles, it’s so much.”

“Yeah, I know. You’re so full right now, and you love it, don’t you? Like being caught between us, fucking yourselves on our dicks?” Stiles takes Derek’s fists and eases them open, putting their palms together and entwining their fingers. “You can take it, Derek. Just stop thinking about it and let go. Or do you want to stop? We will if it’s too much.”

“No, don’t stop. Please don’t.” Derek sobs as he grips Stiles’ hands tight and falls forward, burying his face against Stiles’ neck. Stiles meets Jackson’s heated gaze over Derek’s back, watches Jackson stroke the curves of Derek’s tattoo as he makes shallow thrusts until Derek’s ass stretches enough for him to go deeper. Stiles rolls his hips up, but he isn’t really able to pull out and push in very well from this position. It doesn’t matter considering the friction that he’s getting from Jackson’s dick and the tightness of Derek’s ass. Jackson begins to move faster, pulling out then shoving in, dick squeezing against Stiles’, so tight. 

Stiles kisses Derek’s face, licking away tears and murmuring in his ear. He tells him how beautiful he is, how good he is, how he’s doing so well. They’re kissing when Jackson comes, wet sticky dripping down Stiles’ dick and into Derek’s ass. The first drop makes Derek groan, and Stiles shifts his body so he can rub his belly against Derek’s erection, giving him some kind of friction so he can come, too. It doesn’t take much, not with Jackson coming in his ass and Stiles fucking up into him a little harder, a little faster. Stiles manages to hold off until Derek is coming, ropes of come dripping onto his skin as Derek makes these beautiful noises even as he bites his swollen lips. Stiles comes hard, grunting as he bucks up, his come joining Jackson’s in Derek’s ass.

Jackson pulls out and strokes Derek’s back before he leans down to kiss Stiles. He brushes a quick kiss against his Derek’s mouth before he rolls off the bed. “You don’t have to…” Stiles starts to tell him, but he trails off because he isn’t that surprised that Jackson wants to get out of here before it the afterglow wears off and any emotions might begin. “Thanks, Jackson.”

“He’s leaving already?” Derek manages to ask, his voice low and his eyes slightly dazed. He looks so fucking gorgeous when he’s totally fucked out.

“Yeah, sorry, but I’ve got somewhere else to be,” Jackson says, pulling on his pants without even bothering with his underwear. He grabs his shirt and winks at them. “If you ever need a third dick again, you’ve know my number.”

“I’ll call you soon for lunch,” Stiles tells him, stroking Derek’s hair and holding him tight as he comes down from his high. “Love ya.”

“Yeah, yeah. Of course you do.” Jackson smiles slightly. “Back at ya. Take care of your boy. He’s done in.”

“I will. Lock up when you leave, would you? And don’t forget your leftovers.” Stiles watches Jackson go then turns his attention back to Derek. “You okay?”

“No,” Derek whispers. “That was pretty extreme.”

“Did you enjoy it, at least?” Stiles kisses his cheek and rubs his face against Derek’s jaw, letting him mark him with his beard. 

“Yes.” Derek looks at him. “But I don’t think I’d want to do it again. It was too much, but it was exactly what I’ve always imagined. Thank you.”

“Anytime.” Stiles kisses him gently. “And I mean that. Any fantasies, you can tell me about them, and we can decide if they should go on our bucket list or not.”

“I know.” Derek rubs their noses together. “And I mean it when I say that _you are_ my fantasy.”

“I’m glad Jackson managed to escape before we could get all our emotions on him. He’d have sulked for weeks. God, I love you so much,” Stiles murmurs, brushing light kisses all over Derek’s face. Later, when Derek is ready, Stiles will crawl down the bed and lick his ass clean. For now, he’s content with snuggling and enjoying the afterglow for a little longer.

**Author's Note:**

> I'm currently accepting prompts. Just choose a prompt or two from [this list](http://inell.tumblr.com/post/138119657491/my-favorite-tropes-prompt-me) and drop the prompt(s) with a ship in my [ask](http://inell.tumblr.com/ask)!


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